{"drugs": [{"applicants": ["Alembic Pharmaceuticals Ltd", "Novitium Pharma Llc", "Lannett Co Inc", "Msn Laboratories Private Ltd", "Granules Pharmaceuticals Inc", "Mylan Pharmaceuticals Inc", "Appco Pharma Llc", "Ani Pharmaceuticals Inc", "Watson Laboratories Inc", "Teva Pharmaceuticals Usa"], "atc_classification": [{"code": "C02CA01", "description": "CARDIOVASCULAR SYSTEM: ANTIHYPERTENSIVES: ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING: Alpha-adrenoreceptor antagonists"}], "availability_type": 1, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": 1976, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL2", "molecule_properties": {"alogp": "1.78", "aromatic_rings": 3, "full_molformula": "C19H21N5O4", "full_mwt": "383.41", "hba": 8, "hbd": 1, "heavy_atoms": 28, "mw_freebase": "383.41", "np_likeness_score": "-1.29", "num_ro5_violations": 0, "psa": "106.95", "qed_weighted": "0.73", "ro3_pass": "N", "rtb": 4}, "molecule_structures": {"canonical_smiles": "COc1cc2nc(N3CCN(C(=O)c4ccco4)CC3)nc(N)c2cc1OC", "molfile": "\n RDKit 2D\n\n 28 31 0 0 0 0 0 0 0 0999 V2000\n 0.9375 -1.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9292 -2.6917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3208 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2875 -3.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3042 -1.6167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3208 -1.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3917 -0.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5542 -1.6417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7792 -0.9542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9500 -3.0167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0125 -0.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9250 -1.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5833 -2.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5708 -1.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2417 -1.5917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5417 -0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1667 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1667 -0.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7792 -1.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4042 0.0875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5792 -0.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9417 -1.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.1542 -0.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2667 -3.7542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.2000 -2.9917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1833 -1.5792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.7958 -1.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.7958 -2.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 1 2 0\n 3 6 1 0\n 4 2 1 0\n 5 1 1 0\n 6 5 2 0\n 7 9 1 0\n 8 1 1 0\n 9 19 1 0\n 10 3 1 0\n 11 7 1 0\n 12 6 1 0\n 13 14 1 0\n 14 12 2 0\n 15 11 1 0\n 16 8 1 0\n 17 8 1 0\n 18 16 1 0\n 19 17 1 0\n 20 7 2 0\n 21 11 2 0\n 22 15 1 0\n 23 21 1 0\n 24 4 1 0\n 25 13 1 0\n 26 14 1 0\n 27 26 1 0\n 28 25 1 0\n 3 4 2 0\n 9 18 1 0\n 10 13 2 0\n 22 23 2 0\nM END\n", "standard_inchi": "InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)", "standard_inchi_key": "IENZQIKPVFGBNW-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "CP-122991", "syn_type": "RESEARCH_CODE", "synonyms": "CP-122991"}, {"molecule_synonym": "Prazosin", "syn_type": "ATC", "synonyms": "PRAZOSIN"}, {"molecule_synonym": "Prazosin", "syn_type": "BAN", "synonyms": "PRAZOSIN"}, {"molecule_synonym": "Prazosin", "syn_type": "INN", "synonyms": "PRAZOSIN"}, {"molecule_synonym": "Prazosin", "syn_type": "MERCK_INDEX", "synonyms": "PRAZOSIN"}, {"molecule_synonym": "Prazosin", "syn_type": "OTHER", "synonyms": "PRAZOSIN"}, {"molecule_synonym": "Prazosina", "syn_type": "INN_SPANISH", "synonyms": "PRAZOSINA"}, {"molecule_synonym": "Prazosine", "syn_type": "INN_FRENCH", "synonyms": "PRAZOSINE"}], "ob_patent": null, "oral": 1, "parenteral": 0, "prodrug": 0, "research_codes": ["NSC-292810", "CP-12299-1", "CP-12,299-1", "CP-122991"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Prazosin hydrochloride (JAN, MI, USAN, USP)", "Prazosin (BAN, INN, MI)", ""], "topical": 0, "usan_stem": "-azosin", "usan_stem_definition": "antihypertensives (prazosin type)", "usan_stem_substem": "-azosin(-azosin)", "usan_year": 1968, "withdrawn_flag": "0"}, {"applicants": ["Pld Acquisitions Llc Dba Avema Pharma Solutions", "Aveva Drug Delivery Systems Inc", "Ivax Pharmaceuticals Inc Sub Teva Pharmaceuticals Usa", "P And L Development Llc", "Difgen Pharmaceuticals Llc", "Perrigo R And D Co", "Perrigo Pharma International Dac", "Chattem Inc Dba Sanofi Consumer Healthcare", "Mcneil Consumer Healthcare", "Dr Reddys Laboratories Sa"], "atc_classification": [{"code": "N07BA01", "description": "NERVOUS SYSTEM: OTHER NERVOUS SYSTEM DRUGS: DRUGS USED IN ADDICTIVE DISORDERS: Drugs used in nicotine dependence"}], "availability_type": 2, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 1, "drug_type": 1, "first_approval": 1984, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL3", "molecule_properties": {"alogp": "1.85", "aromatic_rings": 1, "full_molformula": "C10H14N2", "full_mwt": "162.24", "hba": 2, "hbd": 0, "heavy_atoms": 12, "mw_freebase": "162.24", "np_likeness_score": "-0.41", "num_ro5_violations": 0, "psa": "16.13", "qed_weighted": "0.63", "ro3_pass": "Y", "rtb": 1}, "molecule_structures": {"canonical_smiles": "CN1CCC[C@H]1c1cccnc1", "molfile": "\n RDKit 2D\n\n 12 13 0 0 1 0 0 0 0 0999 V2000\n 3.3250 -3.3500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7500 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1417 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9042 -3.3792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5167 -3.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9042 -3.7750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3375 -2.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9542 -4.4292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6667 -4.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1417 -2.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9125 -2.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5292 -2.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 1 1 0\n 2 3 1 1\n 4 5 2 0\n 5 3 1 0\n 6 1 1 0\n 7 1 1 0\n 8 2 1 0\n 9 6 1 0\n 10 3 2 0\n 11 12 2 0\n 12 10 1 0\n 9 8 1 0\n 11 4 1 0\nM END\n", "standard_inchi": "InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1", "standard_inchi_key": "SNICXCGAKADSCV-JTQLQIEISA-N"}, "molecule_synonyms": [{"molecule_synonym": "Habitrol", "syn_type": "TRADE_NAME", "synonyms": "HABITROL"}, {"molecule_synonym": "Nicabate", "syn_type": "TRADE_NAME", "synonyms": "NICABATE"}, {"molecule_synonym": "Nicoderm cq", "syn_type": "TRADE_NAME", "synonyms": "NICODERM CQ"}, {"molecule_synonym": "Nicopass", "syn_type": "TRADE_NAME", "synonyms": "NICOPASS"}, {"molecule_synonym": "Nicopatch", "syn_type": "TRADE_NAME", "synonyms": "NICOPATCH"}, {"molecule_synonym": "Nicorette invisi", "syn_type": "TRADE_NAME", "synonyms": "NICORETTE INVISI"}, {"molecule_synonym": "Nicotine", "syn_type": "ATC", "synonyms": "NICOTINE"}, {"molecule_synonym": "Nicotine", "syn_type": "BNF", "synonyms": "NICOTINE"}, {"molecule_synonym": "Nicotine", "syn_type": "FDA", "synonyms": "NICOTINE"}, {"molecule_synonym": "Nicotine", "syn_type": "MERCK_INDEX", "synonyms": "NICOTINE"}, {"molecule_synonym": "Nicotine", "syn_type": "OTHER", "synonyms": "NICOTINE"}, {"molecule_synonym": "Nicotine", "syn_type": "TRADE_NAME", "synonyms": "NICOTINE"}, {"molecule_synonym": "Nicotine", "syn_type": "USP", "synonyms": "NICOTINE"}, {"molecule_synonym": "Nicotinell classic", "syn_type": "TRADE_NAME", "synonyms": "NICOTINELL CLASSIC"}, {"molecule_synonym": "Nicotinell support", "syn_type": "TRADE_NAME", "synonyms": "NICOTINELL SUPPORT"}, {"molecule_synonym": "Nicotinell tts 10", "syn_type": "TRADE_NAME", "synonyms": "NICOTINELL TTS 10"}, {"molecule_synonym": "Nicotinell tts 20", "syn_type": "TRADE_NAME", "synonyms": "NICOTINELL TTS 20"}, {"molecule_synonym": "Nicotinell tts 30", "syn_type": "TRADE_NAME", "synonyms": "NICOTINELL TTS 30"}, {"molecule_synonym": "Nicotrol", "syn_type": "TRADE_NAME", "synonyms": "NICOTROL"}, {"molecule_synonym": "Nicotrol inhaler", "syn_type": "TRADE_NAME", "synonyms": "Nicotrol Inhaler"}, {"molecule_synonym": "Nicotrol ns", "syn_type": "TRADE_NAME", "synonyms": "Nicotrol NS"}, {"molecule_synonym": "Niquitin", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN"}, {"molecule_synonym": "Niquitin clr", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN CLR"}, {"molecule_synonym": "Niquitin minis cherry", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN MINIS CHERRY"}, {"molecule_synonym": "Niquitin minis mint", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN MINIS MINT"}, {"molecule_synonym": "Niquitin minis orange", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN MINIS ORANGE"}, {"molecule_synonym": "Niquitin mint", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN MINT"}, {"molecule_synonym": "Niquitin pre-quit", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN PRE-QUIT"}, {"molecule_synonym": "Niquitin strips mint", "syn_type": "TRADE_NAME", "synonyms": "NIQUITIN STRIPS MINT"}, {"molecule_synonym": "Prostep", "syn_type": "TRADE_NAME", "synonyms": "PROSTEP"}, {"molecule_synonym": "Stoppers", "syn_type": "TRADE_NAME", "synonyms": "STOPPERS"}, {"molecule_synonym": "Stubit", "syn_type": "TRADE_NAME", "synonyms": "STUBIT"}], "ob_patent": "8323683", "oral": 1, "parenteral": 0, "prodrug": 0, "research_codes": ["NSC-97238"], "rule_of_five": 1, "sc_patent": "US-8323683-B2", "synonyms": ["Nicotine bitartrate (MI, USAN)", "Nicotine bitartrate dihydrate (USP)", "Nicotine (MI, USP)", "Nicotine polacrilex (USAN, USP)", ""], "topical": 1, "usan_stem": null, "usan_stem_definition": null, "usan_stem_substem": null, "usan_year": 1985, "withdrawn_flag": "0"}, {"applicants": null, "atc_code_description": null, "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 1, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "1.0", "molecule_chembl_id": "CHEMBL6200", "molecule_properties": {"alogp": "1.51", "aromatic_rings": 1, "full_molformula": "C9H12N2", "full_mwt": "148.21", "hba": 2, "hbd": 1, "heavy_atoms": 11, "mw_freebase": "148.21", "np_likeness_score": "-0.09", "num_ro5_violations": 0, "psa": "24.92", "qed_weighted": "0.65", "ro3_pass": "Y", "rtb": 1}, "molecule_structures": {"canonical_smiles": "c1cncc([C@@H]2CCCN2)c1", "molfile": "\n RDKit 2D\n\n 11 12 0 0 0 0 0 0 0 0999 V2000\n 6.8984 -4.7940 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4277 -4.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1426 -4.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7185 -6.1312 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4277 -5.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4482 -4.1720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7185 -4.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0036 -5.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2200 -3.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.0036 -4.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0249 -3.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3 2 1 6\n 3 1 1 0\n 4 5 2 0\n 5 2 1 0\n 6 1 1 0\n 7 2 2 0\n 8 10 2 0\n 9 3 1 0\n 10 7 1 0\n 11 6 1 0\n 9 11 1 0\n 4 8 1 0\nM END", "standard_inchi": "InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1", "standard_inchi_key": "MYKUKUCHPMASKF-VIFPVBQESA-N"}, "molecule_synonyms": [{"molecule_synonym": "1'-demethylnicotine", "syn_type": "OTHER", "synonyms": "1'-DEMETHYLNICOTINE"}, {"molecule_synonym": "3-(2-pyrrolidinyl)-(s)-pyridine", "syn_type": "OTHER", "synonyms": "3-(2-PYRROLIDINYL)-(S)-PYRIDINE"}, {"molecule_synonym": "Nicotine related compound f", "syn_type": "OTHER", "synonyms": "NICOTINE RELATED COMPOUND F"}, {"molecule_synonym": "Nornicotine", "syn_type": "MERCK_INDEX", "synonyms": "NORNICOTINE"}, {"molecule_synonym": "Nornicotine", "syn_type": "OTHER", "synonyms": "NORNICOTINE"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": null, "rule_of_five": 1, "sc_patent": null, "synonyms": ["Nornicotine (MI)", ""], "topical": 0, "usan_stem": null, "usan_stem_definition": null, "usan_stem_substem": null, "usan_year": null, "withdrawn_flag": "0"}, {"applicants": ["Somerset Therapeutics Llc", "Ranbaxy Laboratories Ltd", "Janssen Pharmaceuticals Inc", "Teva Pharmaceuticals Usa Inc", "Sandoz Inc", "Daiichi Pharmaceutical Corp", "Ortho Mcneil Pharmaceutical Inc", "Allergan Inc", "Bedford Laboratories Div Ben Venue Laboratories Inc", "Dr Reddys Laboratories Ltd"], "atc_classification": [{"code": "S01AE01", "description": "SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFECTIVES: Fluoroquinolone"}, {"code": "J01MA01", "description": "ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolone"}, {"code": "S02AA16", "description": "SENSORY ORGANS: OTOLOGICALS: ANTIINFECTIVES: Antiinfectives"}], "availability_type": 1, "biotherapeutic": null, "black_box": 1, "black_box_warning": "1", "chirality": 0, "drug_type": 1, "first_approval": 1990, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL4", "molecule_properties": {"alogp": "1.54", "aromatic_rings": 2, "full_molformula": "C18H20FN3O4", "full_mwt": "361.37", "hba": 6, "hbd": 1, "heavy_atoms": 26, "mw_freebase": "361.37", "np_likeness_score": "-0.21", "num_ro5_violations": 0, "psa": "75.01", "qed_weighted": "0.87", "ro3_pass": "N", "rtb": 2}, "molecule_structures": {"canonical_smiles": "CC1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23", "molfile": "\n RDKit 2D\n\n 26 29 0 0 0 0 0 0 0 0999 V2000\n 3.0250 -1.8625 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6417 -2.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4042 -2.2250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7875 -1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4167 -2.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6375 -2.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0292 -3.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1792 -2.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7875 -1.1625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.1792 -2.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8042 -3.2917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5542 -1.8792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2583 -3.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0167 -1.1542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.6833 -1.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0375 -3.9917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3917 -0.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0583 -2.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5500 -1.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2625 -3.9875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5667 -3.3042 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n -0.6750 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0708 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8708 -2.9208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.3000 -0.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6292 -0.7875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 6 2 0\n 3 1 1 0\n 4 3 1 0\n 5 3 2 0\n 6 1 1 0\n 7 2 1 0\n 8 4 2 0\n 9 17 1 0\n 10 8 1 0\n 11 5 1 0\n 12 8 1 0\n 13 2 1 0\n 14 1 1 0\n 15 23 1 0\n 16 7 2 0\n 17 14 1 0\n 18 12 1 0\n 19 12 1 0\n 20 13 2 0\n 21 10 1 0\n 22 18 1 0\n 23 19 1 0\n 24 13 1 0\n 25 15 1 0\n 26 14 1 0\n 5 7 1 0\n 4 9 1 0\n 11 10 2 0\n 15 22 1 0\nM END\n", "standard_inchi": "InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)", "standard_inchi_key": "GSDSWSVVBLHKDQ-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "DL-8280", "syn_type": "RESEARCH_CODE", "synonyms": "DL-8280"}, {"molecule_synonym": "Exocin", "syn_type": "TRADE_NAME", "synonyms": "EXOCIN"}, {"molecule_synonym": "Floxin", "syn_type": "TRADE_NAME", "synonyms": "FLOXIN"}, {"molecule_synonym": "Floxin otic", "syn_type": "TRADE_NAME", "synonyms": "FLOXIN OTIC"}, {"molecule_synonym": "HOE 280", "syn_type": "RESEARCH_CODE", "synonyms": "HOE 280"}, {"molecule_synonym": "HOE-280", "syn_type": "RESEARCH_CODE", "synonyms": "HOE-280"}, {"molecule_synonym": "J01MA01", "syn_type": "RESEARCH_CODE", "synonyms": "J01MA01"}, {"molecule_synonym": "NSC-727071", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-727071"}, {"molecule_synonym": "NSC-758178", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-758178"}, {"molecule_synonym": "Ocuflox", "syn_type": "TRADE_NAME", "synonyms": "OCUFLOX"}, {"molecule_synonym": "Ofloxacin", "syn_type": "ATC", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "BAN", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "BNF", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "FDA", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "INN", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "JAN", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "MERCK_INDEX", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "OTHER", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "TRADE_NAME", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "USAN", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacin", "syn_type": "USP", "synonyms": "OFLOXACIN"}, {"molecule_synonym": "Ofloxacine", "syn_type": "INN_FRENCH", "synonyms": "OFLOXACINE"}, {"molecule_synonym": "Ofloxacino", "syn_type": "INN_SPANISH", "synonyms": "OFLOXACINO"}, {"molecule_synonym": "Tarivid", "syn_type": "TRADE_NAME", "synonyms": "TARIVID"}, {"molecule_synonym": "Tarivid 400", "syn_type": "TRADE_NAME", "synonyms": "TARIVID 400"}, {"molecule_synonym": "Tarivid i.v.", "syn_type": "TRADE_NAME", "synonyms": "TARIVID I.V."}, {"molecule_synonym": "Visiren", "syn_type": "TRADE_NAME", "synonyms": "Visiren"}], "ob_patent": null, "oral": 1, "parenteral": 1, "prodrug": 0, "research_codes": ["DL-8280", "J01MA01", "NSC-727071", "HOE 280", "HOE-280", "NSC-758178"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Ofloxacin (BAN, INN, JAN, MI, USAN, USP)", ""], "topical": 1, "usan_stem": "-oxacin", "usan_stem_definition": "antibacterials (quinolone derivatives)", "usan_stem_substem": "-oxacin(-oxacin)", "usan_year": 1984, "withdrawn_flag": "0"}, {"applicants": ["Sanofi Aventis Us Llc", "Watson Laboratories Inc", "Sun Pharmaceutical Industries Inc"], "atc_classification": [{"code": "J01MB02", "description": "ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Other quinolones"}], "availability_type": 0, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": 1964, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL5", "molecule_properties": {"alogp": "1.42", "aromatic_rings": 2, "full_molformula": "C12H12N2O3", "full_mwt": "232.24", "hba": 4, "hbd": 1, "heavy_atoms": 17, "mw_freebase": "232.24", "np_likeness_score": "-0.98", "num_ro5_violations": 0, "psa": "72.19", "qed_weighted": "0.85", "ro3_pass": "N", "rtb": 2}, "molecule_structures": {"canonical_smiles": "CCn1cc(C(=O)O)c(=O)c2ccc(C)nc21", "molfile": "\n RDKit 2D\n\n 17 18 0 0 0 0 0 0 0 0999 V2000\n 4.2125 -4.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4375 -4.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4417 -4.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8250 -3.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8292 -5.1875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2167 -4.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0625 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5917 -3.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0542 -3.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8250 -3.0542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6042 -3.0542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6750 -4.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9625 -4.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6667 -4.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.8250 -5.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2917 -5.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2167 -6.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 4 1 0\n 3 5 1 0\n 4 1 1 0\n 5 6 1 0\n 6 1 2 0\n 7 3 1 0\n 8 1 1 0\n 9 2 1 0\n 10 4 2 0\n 11 8 2 0\n 12 7 2 0\n 13 8 1 0\n 14 9 2 0\n 15 5 1 0\n 16 12 1 0\n 17 15 1 0\n 2 3 2 0\n 14 12 1 0\nM END\n", "standard_inchi": "InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)", "standard_inchi_key": "MHWLWQUZZRMNGJ-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Acide nalidixique", "syn_type": "INN_FRENCH", "synonyms": "ACIDE NALIDIXIQUE"}, {"molecule_synonym": "Acido nalidixico", "syn_type": "INN_SPANISH", "synonyms": "ACIDO NALIDIXICO"}, {"molecule_synonym": "Mictral", "syn_type": "TRADE_NAME", "synonyms": "MICTRAL"}, {"molecule_synonym": "Nalidixane", "syn_type": "OTHER", "synonyms": "NALIDIXANE"}, {"molecule_synonym": "Nalidixate", "syn_type": "OTHER", "synonyms": "NALIDIXATE"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "ATC", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "BAN", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "BNF", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "FDA", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "INN", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "JAN", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "MERCK_INDEX", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "OTHER", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "TRADE_NAME", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "USAN", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalidixic acid", "syn_type": "USP", "synonyms": "NALIDIXIC ACID"}, {"molecule_synonym": "Nalix", "syn_type": "TRADE_NAME", "synonyms": "NALIX"}, {"molecule_synonym": "Neg gram", "syn_type": "TRADE_NAME", "synonyms": "Neg Gram"}, {"molecule_synonym": "Neggram", "syn_type": "TRADE_NAME", "synonyms": "NEGGRAM"}, {"molecule_synonym": "Negram", "syn_type": "TRADE_NAME", "synonyms": "NEGRAM"}, {"molecule_synonym": "NSC-82174", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-82174"}, {"molecule_synonym": "Uriben", "syn_type": "TRADE_NAME", "synonyms": "URIBEN"}, {"molecule_synonym": "Uroneg", "syn_type": "TRADE_NAME", "synonyms": "Uroneg"}, {"molecule_synonym": "WIN 18,320", "syn_type": "RESEARCH_CODE", "synonyms": "WIN 18,320"}, {"molecule_synonym": "WIN-18320", "syn_type": "RESEARCH_CODE", "synonyms": "WIN-18320"}], "ob_patent": null, "oral": 1, "parenteral": 0, "prodrug": 0, "research_codes": ["NSC-82174", "WIN-18320", "WIN 18,320-3", "WIN-18320-3", "WIN 18,320"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Nalidixate sodium (USAN)", "Nalidixic acid (BAN, INN, JAN, MI, USAN, USP)", ""], "topical": 0, "usan_stem": "nal-", "usan_stem_definition": "narcotic agonists/antagonists (normorphine type)", "usan_stem_substem": "nal-(nal-)", "usan_year": 1962, "withdrawn_flag": "0"}, {"applicants": null, "atc_code_description": null, "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "2.0", "molecule_chembl_id": "CHEMBL6246", "molecule_properties": {"alogp": "1.31", "aromatic_rings": 4, "full_molformula": "C14H6O8", "full_mwt": "302.19", "hba": 8, "hbd": 4, "heavy_atoms": 22, "mw_freebase": "302.19", "np_likeness_score": "1.07", "num_ro5_violations": 0, "psa": "141.34", "qed_weighted": "0.22", "ro3_pass": "N", "rtb": 0}, "molecule_structures": {"canonical_smiles": "O=c1oc2c(O)c(O)cc3c(=O)oc4c(O)c(O)cc1c4c23", "molfile": "\n RDKit 2D\n\n 22 25 0 0 0 0 0 0 0 0999 V2000\n -0.4750 -0.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5750 0.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4750 -1.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5750 1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5333 0.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6292 -0.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.5750 -2.0875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4750 2.2083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5333 1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6292 -1.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6292 2.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5333 -2.0875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5833 -0.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6792 0.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5833 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6792 1.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5625 2.2208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.6625 -2.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6292 3.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.5333 -3.2917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6375 -2.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7375 2.1208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2 1 1 0\n 3 1 1 0\n 4 2 2 0\n 5 1 2 0\n 6 2 1 0\n 7 3 1 0\n 8 9 1 0\n 9 5 1 0\n 10 7 1 0\n 11 4 1 0\n 12 3 2 0\n 13 5 1 0\n 14 6 2 0\n 15 13 2 0\n 16 14 1 0\n 17 9 2 0\n 18 10 2 0\n 19 11 1 0\n 20 12 1 0\n 21 15 1 0\n 22 16 1 0\n 12 15 1 0\n 4 8 1 0\n 6 10 1 0\n 11 16 2 0\nM END\n", "standard_inchi": "InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H", "standard_inchi_key": "AFSDNFLWKVMVRB-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Acide ellagique", "syn_type": "INN_FRENCH", "synonyms": "ACIDE ELLAGIQUE"}, {"molecule_synonym": "Acido elagico", "syn_type": "INN_SPANISH", "synonyms": "ACIDO ELAGICO"}, {"molecule_synonym": "Ellagic acid", "syn_type": "INN", "synonyms": "ELLAGIC ACID"}, {"molecule_synonym": "Ellagic acid", "syn_type": "OTHER", "synonyms": "ELLAGIC ACID"}, {"molecule_synonym": "NSC-407286", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-407286"}, {"molecule_synonym": "NSC-656272", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-656272"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": ["NSC-656272", "NSC-407286"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Ellagic acid (INN)", ""], "topical": 0, "usan_stem": null, "usan_stem_definition": null, "usan_stem_substem": null, "usan_year": null, "withdrawn_flag": "0"}, {"applicants": null, "atc_code_description": null, "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "3.0", "molecule_chembl_id": "CHEMBL204021", "molecule_properties": {"alogp": "7.22", "aromatic_rings": 4, "full_molformula": "C36H38F4N4O2S", "full_mwt": "666.79", "hba": 6, "hbd": 0, "heavy_atoms": 47, "mw_freebase": "666.79", "np_likeness_score": "-1.74", "num_ro5_violations": 2, "psa": "58.44", "qed_weighted": "0.09", "ro3_pass": "N", "rtb": 13}, "molecule_structures": {"canonical_smiles": "CCN(CC)CCN(Cc1ccc(-c2ccc(C(F)(F)F)cc2)cc1)C(=O)Cn1c(SCc2ccc(F)cc2)nc(=O)c2c1CCC2", "molfile": "\n RDKit 2D\n\n 47 51 0 0 0 0 0 0 0 0999 V2000\n -8.6036 -1.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -9.3181 -1.7973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -9.3181 -2.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -8.6036 -3.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.8891 -2.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.8891 -1.7973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -10.0325 -1.3848 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n -7.1746 -3.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.4601 -2.6223 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n -6.4601 -1.7973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.7457 -1.3848 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -5.7457 -0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -6.4601 -0.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.1746 -0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -7.1746 -1.3848 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -7.8891 -0.1473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -6.2886 0.6596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.4681 0.7459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.1326 -0.0077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.0312 -1.7973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3167 -1.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6023 -1.7973 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.8878 -1.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6023 -2.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3167 -0.5598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3167 -3.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3167 -3.8598 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -5.0312 -4.2723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6023 -4.2723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.8878 -3.8598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -5.7457 -3.8598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1733 -1.7973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1733 -2.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4589 -3.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7444 -2.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.7444 -1.7973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4588 -1.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0299 -3.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0299 -3.8598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6846 -4.2723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3990 -3.8598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.3991 -3.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6846 -2.6223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1135 -4.2723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8280 -3.8598 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1135 -5.0973 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8280 -4.6848 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 1 6 2 0\n 2 3 2 0\n 3 4 1 0\n 4 5 2 0\n 5 6 1 0\n 2 7 1 0\n 5 8 1 0\n 8 9 1 0\n 9 10 1 0\n 10 11 1 0\n 15 10 2 0\n 11 12 1 0\n 13 14 1 0\n 14 15 1 0\n 14 16 2 0\n 12 19 1 0\n 12 13 2 0\n 13 17 1 0\n 17 18 1 0\n 18 19 1 0\n 11 20 1 0\n 20 21 1 0\n 21 22 1 0\n 22 23 1 0\n 22 24 1 0\n 21 25 2 0\n 24 26 1 0\n 26 27 1 0\n 27 28 1 0\n 27 29 1 0\n 29 30 1 0\n 28 31 1 0\n 23 32 1 0\n 32 33 1 0\n 32 37 2 0\n 33 34 2 0\n 34 35 1 0\n 35 36 2 0\n 36 37 1 0\n 35 38 1 0\n 38 39 1 0\n 38 43 2 0\n 39 40 2 0\n 40 41 1 0\n 41 42 2 0\n 42 43 1 0\n 41 44 1 0\n 44 45 1 0\n 44 46 1 0\n 44 47 1 0\nM END\n", "standard_inchi": "InChI=1S/C36H38F4N4O2S/c1-3-42(4-2)20-21-43(22-25-8-12-27(13-9-25)28-14-16-29(17-15-28)36(38,39)40)33(45)23-44-32-7-5-6-31(32)34(46)41-35(44)47-24-26-10-18-30(37)19-11-26/h8-19H,3-7,20-24H2,1-2H3", "standard_inchi_key": "WDPFJWLDPVQCAJ-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Darapladib", "syn_type": "INN", "synonyms": "DARAPLADIB"}, {"molecule_synonym": "Darapladib", "syn_type": "JAN", "synonyms": "DARAPLADIB"}, {"molecule_synonym": "Darapladib", "syn_type": "MERCK_INDEX", "synonyms": "DARAPLADIB"}, {"molecule_synonym": "Darapladib", "syn_type": "OTHER", "synonyms": "DARAPLADIB"}, {"molecule_synonym": "Darapladib", "syn_type": "USAN", "synonyms": "DARAPLADIB"}, {"molecule_synonym": "SB-480848", "syn_type": "RESEARCH_CODE", "synonyms": "SB-480848"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": ["SB-480848"], "rule_of_five": 0, "sc_patent": null, "synonyms": ["Darapladib (INN, JAN, MI, USAN)", ""], "topical": 0, "usan_stem": "-pladib", "usan_stem_definition": "phospholipase A2 inhibitors", "usan_stem_substem": "-pladib(-pladib)", "usan_year": 2005, "withdrawn_flag": "0"}, {"applicants": ["Novitium Pharma Llc", "Cosette Pharmaceuticals Inc", "Genus Lifesciences Inc", "Heritage Pharma Labs Inc", "Aurobindo Pharma Ltd", "Teva Pharmaceuticals Usa Inc", "Mutual Pharmaceutical Co Inc", "Cycle Pharmaceuticals Ltd", "Inwood Laboratories Inc Sub Forest Laboratories Inc", "Rising Pharma Holdings Inc"], "atc_classification": [{"code": "S01BC01", "description": "SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFLAMMATORY AGENTS: Antiinflammatory agents, non-steroid"}, {"code": "C01EB03", "description": "CARDIOVASCULAR SYSTEM: CARDIAC THERAPY: OTHER CARDIAC PREPARATIONS: Other cardiac preparation"}, {"code": "M01AB01", "description": "MUSCULO-SKELETAL SYSTEM: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS: Acetic acid derivatives and related substance"}, {"code": "M02AA23", "description": "MUSCULO-SKELETAL SYSTEM: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN: Antiinflammatory preparations, non-steroids for topical us"}, {"code": "M01AB51", "description": "MUSCULO-SKELETAL SYSTEM: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS: Acetic acid derivatives and related substances"}], "availability_type": 1, "biotherapeutic": null, "black_box": 1, "black_box_warning": "1", "chirality": 2, "drug_type": 1, "first_approval": 1965, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL6", "molecule_properties": {"alogp": "3.93", "aromatic_rings": 3, "full_molformula": "C19H16ClNO4", "full_mwt": "357.79", "hba": 4, "hbd": 1, "heavy_atoms": 25, "mw_freebase": "357.79", "np_likeness_score": "-0.72", "num_ro5_violations": 0, "psa": "68.53", "qed_weighted": "0.77", "ro3_pass": "N", "rtb": 4}, "molecule_structures": {"canonical_smiles": "COc1ccc2c(c1)c(CC(=O)O)c(C)n2C(=O)c1ccc(Cl)cc1", "molfile": "\n RDKit 2D\n\n 25 27 0 0 0 0 0 0 0 0999 V2000\n 0.6375 -2.8667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0625 -3.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6417 -4.0167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0333 -3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0333 -3.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6292 -2.1542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.6375 -4.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.6458 -2.7375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2417 -1.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2500 -5.0792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.6458 -4.1542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.0125 -1.8042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2417 -5.7917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8542 -2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2292 -1.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7667 -3.4292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2583 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2583 -3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4542 -1.0750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8667 -4.7375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.8375 -0.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4667 -1.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0667 -0.7125 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0\n -1.8708 -4.1542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4875 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 1 1 0\n 3 2 2 0\n 4 1 1 0\n 5 4 1 0\n 6 1 1 0\n 7 3 1 0\n 8 4 2 0\n 9 6 1 0\n 10 7 1 0\n 11 5 2 0\n 12 6 2 0\n 13 10 2 0\n 14 9 2 0\n 15 9 1 0\n 16 2 1 0\n 17 18 2 0\n 18 8 1 0\n 19 21 1 0\n 20 10 1 0\n 21 15 2 0\n 22 14 1 0\n 23 19 1 0\n 24 17 1 0\n 25 24 1 0\n 5 3 1 0\n 22 19 2 0\n 11 17 1 0\nM END\n", "standard_inchi": "InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)", "standard_inchi_key": "CGIGDMFJXJATDK-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Aconip", "syn_type": "OTHER", "synonyms": "ACONIP"}, {"molecule_synonym": "Artracin", "syn_type": "TRADE_NAME", "synonyms": "ARTRACIN"}, {"molecule_synonym": "Artracin sr", "syn_type": "TRADE_NAME", "synonyms": "ARTRACIN SR"}, {"molecule_synonym": "Berlind 75 ret", "syn_type": "TRADE_NAME", "synonyms": "BERLIND 75 RET"}, {"molecule_synonym": "Durametacin", "syn_type": "OTHER", "synonyms": "DURAMETACIN"}, {"molecule_synonym": "Flexin-25 continus", "syn_type": "TRADE_NAME", "synonyms": "FLEXIN-25 CONTINUS"}, {"molecule_synonym": "Flexin-50 continus", "syn_type": "TRADE_NAME", "synonyms": "FLEXIN-50 CONTINUS"}, {"molecule_synonym": "Flexin-75 continus", "syn_type": "TRADE_NAME", "synonyms": "FLEXIN-75 CONTINUS"}, {"molecule_synonym": "Imbrilon", "syn_type": "TRADE_NAME", "synonyms": "IMBRILON"}, {"molecule_synonym": "Indocid-r", "syn_type": "TRADE_NAME", "synonyms": "INDOCID-R"}, {"molecule_synonym": "Indocid ret", "syn_type": "TRADE_NAME", "synonyms": "INDOCID RET"}, {"molecule_synonym": "Indocin", "syn_type": "TRADE_NAME", "synonyms": "INDOCIN"}, {"molecule_synonym": "Indocin sr", "syn_type": "TRADE_NAME", "synonyms": "INDOCIN SR"}, {"molecule_synonym": "Indoderm", "syn_type": "TRADE_NAME", "synonyms": "INDODERM"}, {"molecule_synonym": "Indoflex", "syn_type": "TRADE_NAME", "synonyms": "INDOFLEX"}, {"molecule_synonym": "Indolar", "syn_type": "TRADE_NAME", "synonyms": "INDOLAR"}, {"molecule_synonym": "Indolar sr", "syn_type": "TRADE_NAME", "synonyms": "INDOLAR SR"}, {"molecule_synonym": "Indo-lemmon", "syn_type": "TRADE_NAME", "synonyms": "INDO-LEMMON"}, {"molecule_synonym": "Indomax-25", "syn_type": "TRADE_NAME", "synonyms": "INDOMAX-25"}, {"molecule_synonym": "Indomax-75 sr", "syn_type": "TRADE_NAME", "synonyms": "INDOMAX-75 SR"}, {"molecule_synonym": "Indometacin", "syn_type": "ATC", "synonyms": "INDOMETACIN"}, {"molecule_synonym": "Indometacin", "syn_type": "BAN", "synonyms": "INDOMETACIN"}, {"molecule_synonym": "Indometacin", "syn_type": "BNF", "synonyms": "INDOMETACIN"}, {"molecule_synonym": "Indometacin", "syn_type": "DCF", "synonyms": "INDOMETACIN"}, {"molecule_synonym": "Indometacin", "syn_type": "INN", "synonyms": "INDOMETACIN"}, {"molecule_synonym": "Indometacin", "syn_type": "JAN", "synonyms": "INDOMETACIN"}, {"molecule_synonym": "Indometacin", "syn_type": "OTHER", "synonyms": "INDOMETACIN"}, {"molecule_synonym": "Indometacina", "syn_type": "INN_SPANISH", "synonyms": "INDOMETACINA"}, {"molecule_synonym": "Indometacine", "syn_type": "INN_FRENCH", "synonyms": "INDOMETACINE"}, {"molecule_synonym": "Indometacin farnesil", "syn_type": "JAN", "synonyms": "INDOMETACIN FARNESIL"}, {"molecule_synonym": "Indometacinum", "syn_type": "OTHER", "synonyms": "INDOMETACINUM"}, {"molecule_synonym": "Indomethacin", "syn_type": "FDA", "synonyms": "INDOMETHACIN"}, {"molecule_synonym": "Indomethacin", "syn_type": "MERCK_INDEX", "synonyms": "INDOMETHACIN"}, {"molecule_synonym": "Indomethacin", "syn_type": "OTHER", "synonyms": "INDOMETHACIN"}, {"molecule_synonym": "Indomethacin", "syn_type": "TRADE_NAME", "synonyms": "INDOMETHACIN"}, {"molecule_synonym": "Indomethacin", "syn_type": "USAN", "synonyms": "INDOMETHACIN"}, {"molecule_synonym": "Indomethacin", "syn_type": "USP", "synonyms": "INDOMETHACIN"}, {"molecule_synonym": "Indomod", "syn_type": "TRADE_NAME", "synonyms": "INDOMOD"}, {"molecule_synonym": "Indo-paed", "syn_type": "TRADE_NAME", "synonyms": "INDO-PAED"}, {"molecule_synonym": "Indoptol", "syn_type": "TRADE_NAME", "synonyms": "INDOPTOL"}, {"molecule_synonym": "Indotard mr 75", "syn_type": "TRADE_NAME", "synonyms": "INDOTARD MR 75"}, {"molecule_synonym": "Ledmecin", "syn_type": "TRADE_NAME", "synonyms": "LEDMECIN"}, {"molecule_synonym": "Maximet sr", "syn_type": "TRADE_NAME", "synonyms": "MAXIMET SR"}, {"molecule_synonym": "Mobilan", "syn_type": "TRADE_NAME", "synonyms": "MOBILAN"}, {"molecule_synonym": "NSC-757061", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-757061"}, {"molecule_synonym": "NSC-77541", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-77541"}, {"molecule_synonym": "Pardelprin mr", "syn_type": "TRADE_NAME", "synonyms": "PARDELPRIN MR"}, {"molecule_synonym": "Reumacide", "syn_type": "OTHER", "synonyms": "REUMACIDE"}, {"molecule_synonym": "Rheumacin la", "syn_type": "TRADE_NAME", "synonyms": "RHEUMACIN LA"}, {"molecule_synonym": "Rimacid", "syn_type": "TRADE_NAME", "synonyms": "RIMACID"}, {"molecule_synonym": "Slo-indo", "syn_type": "TRADE_NAME", "synonyms": "SLO-INDO"}, {"molecule_synonym": "Tivorbex", "syn_type": "TRADE_NAME", "synonyms": "TIVORBEX"}], "ob_patent": "8734847", "oral": 1, "parenteral": 1, "prodrug": 0, "research_codes": ["NSC-77541", "NSC-757061"], "rule_of_five": 1, "sc_patent": "US-8734847-B2", "synonyms": ["Indometacin sodium (JAN)", "Indometacin sodium hydrate (JAN)", "Indomethacin sodium (USAN, USP)", "Indomethacin sodium salt trihydrate (MI)", "Indometacin (BAN, DCF, INN, JAN)", "Indometacin farnesil (JAN)", "Indomethacin (MI, USAN, USP)", ""], "topical": 1, "usan_stem": null, "usan_stem_definition": null, "usan_stem_substem": null, "usan_year": 1963, "withdrawn_flag": "0"}, {"applicants": ["Antibiotice Sa", "Istituto Biochimico Italiano Spa", "Sandoz Inc", "Acs Dobfar Spa", "Hospira Inc", "Entasis Therapeutics Inc", "Pfizer Inc", "Steriscience Specialities Pte Ltd", "Pfizer Laboratories Div Pfizer Inc", "Hq Specialty Pharma Corp"], "atc_classification": [{"code": "J01CG01", "description": "ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: BETA-LACTAM ANTIBACTERIALS, PENICILLINS: Beta-lactamase inhibitors"}], "availability_type": 1, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 1, "drug_type": 1, "first_approval": 1986, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL403", "molecule_properties": {"alogp": "-0.79", "aromatic_rings": 0, "full_molformula": "C8H11NO5S", "full_mwt": "233.24", "hba": 4, "hbd": 1, "heavy_atoms": 15, "mw_freebase": "233.24", "np_likeness_score": "0.77", "num_ro5_violations": 0, "psa": "91.75", "qed_weighted": "0.60", "ro3_pass": "N", "rtb": 1}, "molecule_structures": {"canonical_smiles": "CC1(C)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O", "molfile": "\n RDKit 2D\n\n 16 17 0 0 1 0 0 0 0 0999 V2000\n 3.9417 -0.6292 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2667 -1.5542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3583 -1.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2667 -0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9417 -1.7750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5625 -1.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5625 -0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9375 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5792 -0.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2917 -0.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0583 -2.0583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.5458 -2.8417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3167 -2.8292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9667 -1.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9667 -0.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2625 -0.1375 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2 4 1 0\n 3 1 1 0\n 4 1 1 0\n 5 3 1 0\n 6 7 1 0\n 7 4 1 0\n 5 8 1 6\n 9 1 2 0\n 10 1 2 0\n 11 6 2 0\n 12 8 1 0\n 13 8 2 0\n 14 3 1 0\n 15 3 1 0\n 4 16 1 6\n 5 2 1 0\n 2 6 1 0\nM END", "standard_inchi": "InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1", "standard_inchi_key": "FKENQMMABCRJMK-RITPCOANSA-N"}, "molecule_synonyms": [{"molecule_synonym": "CP-458992", "syn_type": "RESEARCH_CODE", "synonyms": "CP-458992"}, {"molecule_synonym": "NSC-759886", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-759886"}, {"molecule_synonym": "Sulbactam", "syn_type": "ATC", "synonyms": "SULBACTAM"}, {"molecule_synonym": "Sulbactam", "syn_type": "BAN", "synonyms": "SULBACTAM"}, {"molecule_synonym": "Sulbactam", "syn_type": "INN", "synonyms": "SULBACTAM"}, {"molecule_synonym": "Sulbactam", "syn_type": "MERCK_INDEX", "synonyms": "SULBACTAM"}, {"molecule_synonym": "Sulbactam", "syn_type": "OTHER", "synonyms": "SULBACTAM"}, {"molecule_synonym": "Sulbactam", "syn_type": "USP", "synonyms": "SULBACTAM"}], "ob_patent": "9309245", "oral": 0, "parenteral": 1, "prodrug": 0, "research_codes": ["CP-45899-2", "CP-45899-99", "NSC-759886", "CP-45,899-99", "CP-45,899-2", "CP-458992"], "rule_of_five": 1, "sc_patent": "US-9309245-B2", "synonyms": ["Sulbactam sodium (JAN, USAN, USP)", "Sulbactam sodium salt (MI)", "Sulbactam (BAN, INN, MI, USP)", "Sulbactam benzathine (USAN)", ""], "topical": 0, "usan_stem": "-bactam", "usan_stem_definition": "beta-lactamase inhibitors", "usan_stem_substem": "-bactam(-bactam)", "usan_year": 1980, "withdrawn_flag": "0"}, {"applicants": null, "atc_code_description": null, "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "2.0", "molecule_chembl_id": "CHEMBL6259", "molecule_properties": {"alogp": "2.72", "aromatic_rings": 3, "full_molformula": "C21H19F2N3O3", "full_mwt": "399.40", "hba": 5, "hbd": 1, "heavy_atoms": 29, "mw_freebase": "399.40", "np_likeness_score": "-1.08", "num_ro5_violations": 0, "psa": "65.78", "qed_weighted": "0.73", "ro3_pass": "N", "rtb": 3}, "molecule_structures": {"canonical_smiles": "CN1CCN(c2cc3c(cc2F)c(=O)c(C(=O)O)cn3-c2ccc(F)cc2)CC1", "molfile": "\n RDKit 2D\n\n 29 32 0 0 0 0 0 0 0 0999 V2000\n -1.7985 -1.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0840 0.0284 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3696 -1.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3696 -0.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0840 -1.6216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7985 -0.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3449 0.0284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0594 -0.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3449 -1.6216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7739 0.0284 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5130 -1.6216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.0594 -1.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0840 0.8534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2028 0.8534 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0840 -2.4466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7739 0.8534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4883 -0.3841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.2274 -1.2091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7985 1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3696 1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.2028 0.0284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4883 1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.7739 -1.6216 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5130 -2.4466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0840 2.5034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.3696 2.0909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7985 2.0909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.0840 3.3284 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 3.9173 1.2659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 4 1 0\n 3 4 2 0\n 1 5 1 0\n 3 5 1 0\n 1 6 2 0\n 2 6 1 0\n 4 7 1 0\n 7 8 2 0\n 3 9 1 0\n 8 10 1 0\n 1 11 1 0\n 8 12 1 0\n 9 12 2 0\n 2 13 1 0\n 5 15 2 0\n 10 16 1 0\n 10 17 1 0\n 11 18 2 0\n 13 19 1 0\n 13 20 2 0\n 14 21 1 0\n 17 21 1 0\n 14 22 1 0\n 16 22 1 0\n 12 23 1 0\n 11 24 1 0\n 20 26 1 0\n 25 26 2 0\n 19 27 2 0\n 25 27 1 0\n 25 28 1 0\n 14 29 1 0\nM END", "standard_inchi": "InChI=1S/C21H19F2N3O3/c1-24-6-8-25(9-7-24)19-11-18-15(10-17(19)23)20(27)16(21(28)29)12-26(18)14-4-2-13(22)3-5-14/h2-5,10-12H,6-9H2,1H3,(H,28,29)", "standard_inchi_key": "NOCJXYPHIIZEHN-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Dicural", "syn_type": "OTHER", "synonyms": "DICURAL"}, {"molecule_synonym": "Difloxacin", "syn_type": "EMA", "synonyms": "DIFLOXACIN"}, {"molecule_synonym": "Difloxacin", "syn_type": "INN", "synonyms": "DIFLOXACIN"}, {"molecule_synonym": "Difloxacine", "syn_type": "INN_FRENCH", "synonyms": "DIFLOXACINE"}, {"molecule_synonym": "Difloxacino", "syn_type": "INN_SPANISH", "synonyms": "DIFLOXACINO"}, {"molecule_synonym": "Pulsaflox", "syn_type": "OTHER", "synonyms": "PULSAFLOX"}, {"molecule_synonym": "Pulsaflox", "syn_type": "TRADE_NAME", "synonyms": "PULSAFLOX"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": ["NSC-759646", "ABBOTT-56619"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Difloxacin (INN)", "Difloxacin hydrochloride (USAN)", "Difloxacin monohydrochloride (MI)", ""], "topical": 0, "usan_stem": "-oxacin", "usan_stem_definition": "antibacterials (quinolone derivatives)", "usan_stem_substem": "-oxacin(-oxacin)", "usan_year": 1986, "withdrawn_flag": "0"}, {"applicants": ["Sandoz Inc", "Istituto Biochimico Italiano Spa", "Fresenius Kabi Usa Llc", "Provepharm Sas", "Fresenius Kabi Anti Infectives Srl", "Hospira Inc", "Astral Steritech Pvt Ltd", "Baxter Healthcare Corp", "Cubist Pharmaceuticals Llc", "Steriscience Specialities Pte Ltd"], "atc_classification": [{"code": "J01CG02", "description": "ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: BETA-LACTAM ANTIBACTERIALS, PENICILLINS: Beta-lactamase inhibitors"}], "availability_type": 1, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 1, "drug_type": 1, "first_approval": 1993, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL404", "molecule_properties": {"alogp": "-1.52", "aromatic_rings": 1, "full_molformula": "C10H12N4O5S", "full_mwt": "300.30", "hba": 7, "hbd": 1, "heavy_atoms": 20, "mw_freebase": "300.30", "np_likeness_score": "-0.31", "num_ro5_violations": 0, "psa": "122.46", "qed_weighted": "0.67", "ro3_pass": "N", "rtb": 3}, "molecule_structures": {"canonical_smiles": "C[C@]1(Cn2ccnn2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O", "molfile": "\n RDKit 2D\n\n 21 23 0 0 1 0 0 0 0 0999 V2000\n 4.7292 -12.8042 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4792 -11.0917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5000 -11.7000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4792 -12.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7042 -10.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1750 -11.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1750 -12.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7042 -10.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.6167 -11.4375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5625 -11.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.0542 -9.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.6917 -11.5792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.5000 -13.4542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.4375 -13.7000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.2167 -12.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.9250 -12.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2542 -10.1667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3667 -8.3042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.1792 -12.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.5875 -9.0792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5750 -13.7125 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 2 4 1 0\n 3 1 1 0\n 4 1 1 0\n 5 3 1 0\n 6 7 1 0\n 7 4 1 0\n 8 9 1 0\n 9 10 1 0\n 10 3 1 0\n 5 11 1 1\n 12 8 2 0\n 13 1 2 0\n 14 1 2 0\n 15 16 2 0\n 16 9 1 0\n 17 6 2 0\n 18 11 2 0\n 3 19 1 1\n 20 11 1 0\n 4 21 1 1\n 5 2 1 0\n 2 6 1 0\n 15 12 1 0\nM END\n", "standard_inchi": "InChI=1S/C10H12N4O5S/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h2-3,7-8H,4-5H2,1H3,(H,16,17)/t7-,8+,10+/m1/s1", "standard_inchi_key": "LPQZKKCYTLCDGQ-WEDXCCLWSA-N"}, "molecule_synonyms": [{"molecule_synonym": "CL 298,741", "syn_type": "RESEARCH_CODE", "synonyms": "CL 298,741"}, {"molecule_synonym": "CL-298741", "syn_type": "RESEARCH_CODE", "synonyms": "CL-298741"}, {"molecule_synonym": "NSC-759887", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-759887"}, {"molecule_synonym": "Tazobactam", "syn_type": "ATC", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "Tazobactam", "syn_type": "BAN", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "Tazobactam", "syn_type": "INN", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "Tazobactam", "syn_type": "JAN", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "Tazobactam", "syn_type": "MERCK_INDEX", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "Tazobactam", "syn_type": "OTHER", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "Tazobactam", "syn_type": "USAN", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "Tazobactam", "syn_type": "USP", "synonyms": "TAZOBACTAM"}, {"molecule_synonym": "YTR-830H", "syn_type": "RESEARCH_CODE", "synonyms": "YTR-830H"}], "ob_patent": "7129232", "oral": 0, "parenteral": 1, "prodrug": 0, "research_codes": ["CL 307,579", "YTR-830H", "CL-307579", "CL-298741", "NSC-759887", "CL 298,741"], "rule_of_five": 1, "sc_patent": "US-7129232-B2", "synonyms": ["Tazobactam sodium (USAN)", "Tazobactam sodium salt (MI)", "Tazobactam (BAN, INN, JAN, MI, USAN, USP)", ""], "topical": 0, "usan_stem": "-bactam", "usan_stem_definition": "beta-lactamase inhibitors", "usan_stem_substem": "-bactam(-bactam)", "usan_year": 1989, "withdrawn_flag": "0"}, {"applicants": null, "atc_classification": [{"code": "J01MA08", "description": "ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolones"}], "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "2.0", "molecule_chembl_id": "CHEMBL6273", "molecule_properties": {"alogp": "1.70", "aromatic_rings": 2, "full_molformula": "C17H18F3N3O3", "full_mwt": "369.34", "hba": 5, "hbd": 1, "heavy_atoms": 26, "mw_freebase": "369.34", "np_likeness_score": "-0.86", "num_ro5_violations": 0, "psa": "65.78", "qed_weighted": "0.89", "ro3_pass": "N", "rtb": 4}, "molecule_structures": {"canonical_smiles": "CN1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(CCF)c3c2F)CC1", "molfile": "\n RDKit 2D\n\n 26 28 0 0 0 0 0 0 0 0999 V2000\n 2.5250 0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8042 0.6833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6542 -0.8042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8042 -0.3042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6542 1.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0458 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5250 -0.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9083 -0.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9083 0.6833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0458 1.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7625 -0.8167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4000 1.1625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.4958 -1.7792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6542 2.1583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5833 -0.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7833 -1.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4042 2.1708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0458 -1.8000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7625 1.1833 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n -3.4833 -0.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6625 -2.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6542 -1.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2667 0.6583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3417 -1.8125 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3458 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4875 -2.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 5 1 0\n 3 7 1 0\n 4 3 1 0\n 5 1 1 0\n 6 4 1 0\n 7 1 2 0\n 8 6 2 0\n 9 10 2 0\n 10 2 1 0\n 11 8 1 0\n 12 1 1 0\n 13 21 1 0\n 14 5 2 0\n 15 11 1 0\n 16 11 1 0\n 17 12 2 0\n 18 6 1 0\n 19 9 1 0\n 20 15 1 0\n 21 16 1 0\n 22 3 1 0\n 23 12 1 0\n 24 26 1 0\n 25 13 1 0\n 26 22 1 0\n 4 2 2 0\n 8 9 1 0\n 20 13 1 0\nM END\n", "standard_inchi": "InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)", "standard_inchi_key": "XBJBPGROQZJDOJ-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "AM-833", "syn_type": "RESEARCH_CODE", "synonyms": "AM-833"}, {"molecule_synonym": "Fleroxacin", "syn_type": "ATC", "synonyms": "FLEROXACIN"}, {"molecule_synonym": "Fleroxacin", "syn_type": "BAN", "synonyms": "FLEROXACIN"}, {"molecule_synonym": "Fleroxacin", "syn_type": "INN", "synonyms": "FLEROXACIN"}, {"molecule_synonym": "Fleroxacin", "syn_type": "JAN", "synonyms": "FLEROXACIN"}, {"molecule_synonym": "Fleroxacin", "syn_type": "USAN", "synonyms": "FLEROXACIN"}, {"molecule_synonym": "Fleroxacine", "syn_type": "INN_FRENCH", "synonyms": "FLEROXACINE"}, {"molecule_synonym": "Fleroxacino", "syn_type": "INN_SPANISH", "synonyms": "FLEROXACINO"}, {"molecule_synonym": "Megalocin", "syn_type": "OTHER", "synonyms": "MEGALOCIN"}, {"molecule_synonym": "Megalone", "syn_type": "TRADE_NAME", "synonyms": "MEGALONE"}, {"molecule_synonym": "RO-236240", "syn_type": "RESEARCH_CODE", "synonyms": "RO-236240"}, {"molecule_synonym": "RO 23-6240/000", "syn_type": "RESEARCH_CODE", "synonyms": "RO 23-6240/000"}, {"molecule_synonym": "RO-23-6240/000", "syn_type": "RESEARCH_CODE", "synonyms": "RO-23-6240/000"}, {"molecule_synonym": "RO-236240000", "syn_type": "RESEARCH_CODE", "synonyms": 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"74.57", "qed_weighted": "0.81", "ro3_pass": "N", "rtb": 6}, "molecule_structures": {"canonical_smiles": "CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(CC)c3c2F)C1", "molfile": "\n RDKit 2D\n\n 27 29 0 0 0 0 0 0 0 0999 V2000\n 2.9542 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5917 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2792 0.6708 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.5917 0.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2792 -0.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9167 0.6708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9542 0.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2417 0.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4250 0.6625 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.2417 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9167 -0.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6167 -0.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.1458 0.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4875 1.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2792 -1.6292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2875 -0.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9167 1.4333 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n -1.6458 0.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.4250 -0.8542 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2792 1.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6292 -1.6000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2375 1.5958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.0333 1.1333 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.3333 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.6375 1.5958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0667 1.7833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3458 1.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 5 1 0\n 3 7 1 0\n 4 3 1 0\n 5 1 1 0\n 6 4 1 0\n 7 1 2 0\n 8 6 2 0\n 9 8 1 0\n 10 11 2 0\n 11 2 1 0\n 12 1 1 0\n 13 9 1 0\n 14 9 1 0\n 15 5 2 0\n 16 12 2 0\n 17 6 1 0\n 18 13 1 0\n 19 10 1 0\n 20 3 1 0\n 21 12 1 0\n 22 14 1 0\n 23 24 1 0\n 24 18 1 0\n 25 23 1 0\n 26 20 1 0\n 27 25 1 0\n 4 2 2 0\n 8 10 1 0\n 18 22 1 0\nM END\n", "standard_inchi": "InChI=1S/C19H23F2N3O3/c1-3-22-8-11-5-6-24(9-11)17-14(20)7-12-16(15(17)21)23(4-2)10-13(18(12)25)19(26)27/h7,10-11,22H,3-6,8-9H2,1-2H3,(H,26,27)", "standard_inchi_key": "BAYYCLWCHFVRLV-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "CI-934", "syn_type": "RESEARCH_CODE", "synonyms": "CI-934"}, {"molecule_synonym": "Merafloxacin", "syn_type": "INN", "synonyms": "MERAFLOXACIN"}, {"molecule_synonym": "Merafloxacine", "syn_type": "INN_FRENCH", "synonyms": "MERAFLOXACINE"}, {"molecule_synonym": "Merafloxacino", "syn_type": "INN_SPANISH", "synonyms": "MERAFLOXACINO"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": ["CI-934"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Merafloxacin (INN)", ""], "topical": 0, "usan_stem": "-oxacin", "usan_stem_definition": "antibacterials (quinolone derivatives)", "usan_stem_substem": "-oxacin(-oxacin)", "usan_year": null, "withdrawn_flag": "0"}, {"applicants": null, "atc_code_description": null, "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "2.0", "molecule_chembl_id": "CHEMBL6231", "molecule_properties": {"alogp": "0.76", "aromatic_rings": 2, "full_molformula": "C16H19FN4O3", "full_mwt": "334.35", "hba": 6, "hbd": 2, "heavy_atoms": 24, "mw_freebase": "334.35", "np_likeness_score": "-0.94", "num_ro5_violations": 0, "psa": "77.81", "qed_weighted": "0.86", "ro3_pass": "N", "rtb": 3}, "molecule_structures": {"canonical_smiles": "CNn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCN(C)CC3)cc21", "molfile": "\n RDKit 2D\n\n 24 26 0 0 0 0 0 0 0 0999 V2000\n 2.5417 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8167 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6792 1.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6792 -0.7917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.8167 -0.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5417 -0.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0375 -0.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9000 -0.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0375 1.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7583 -0.7917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4125 1.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.9000 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.4833 -1.7917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6792 2.1875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6792 -1.7875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7583 -1.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6208 -0.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.4167 2.1875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.6208 -2.2917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.4833 -0.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.7708 1.1958 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2667 0.6958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.3458 -2.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.5375 -2.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 3 1 1 0\n 4 6 1 0\n 5 4 1 0\n 6 1 2 0\n 7 5 1 0\n 8 7 2 0\n 9 2 1 0\n 10 8 1 0\n 11 1 1 0\n 12 9 2 0\n 13 20 1 0\n 14 3 2 0\n 15 4 1 0\n 16 10 1 0\n 17 10 1 0\n 18 11 2 0\n 19 16 1 0\n 20 17 1 0\n 21 12 1 0\n 22 11 1 0\n 23 13 1 0\n 24 15 1 0\n 5 2 2 0\n 8 12 1 0\n 19 13 1 0\nM END\n", "standard_inchi": "InChI=1S/C16H19FN4O3/c1-18-21-9-11(16(23)24)15(22)10-7-12(17)14(8-13(10)21)20-5-3-19(2)4-6-20/h7-9,18H,3-6H2,1-2H3,(H,23,24)", "standard_inchi_key": "RUXPNBWPIRDVTH-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Amifloxacin", "syn_type": "BAN", "synonyms": "AMIFLOXACIN"}, {"molecule_synonym": "Amifloxacin", "syn_type": "INN", "synonyms": "AMIFLOXACIN"}, {"molecule_synonym": "Amifloxacin", "syn_type": "USAN", "synonyms": "AMIFLOXACIN"}, {"molecule_synonym": "Amifloxacine", "syn_type": "INN_FRENCH", "synonyms": "AMIFLOXACINE"}, {"molecule_synonym": "Amifloxacino", "syn_type": "INN_SPANISH", "synonyms": "AMIFLOXACINO"}, {"molecule_synonym": "WIN 49,375", "syn_type": "RESEARCH_CODE", "synonyms": "WIN 49,375"}, {"molecule_synonym": "WIN-49,375", "syn_type": "RESEARCH_CODE", "synonyms": "WIN-49,375"}, {"molecule_synonym": "WIN-49375", "syn_type": "RESEARCH_CODE", "synonyms": "WIN-49375"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": ["WIN 49,375-3", "WIN-49375", "WIN-49375-3", "WIN 49,375", "WIN-49,375"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Amifloxacin mesylate (USAN)", "Amifloxacin (BAN, INN, USAN)", ""], "topical": 0, "usan_stem": "-oxacin", "usan_stem_definition": "antibacterials (quinolone derivatives)", "usan_stem_substem": "-oxacin(-oxacin)", "usan_year": 1984, "withdrawn_flag": "0"}, {"applicants": ["Yiling Pharmaceutical Ltd", "Laboratorios Salvat Sa", "Depomed Inc", "Teva Pharmaceuticals Usa", "Identirx Llc", "Aurobindo Pharma Ltd", "Bayer Healthcare Pharmaceuticals Inc", "Aiping Pharmaceutical Inc", "Nostrum Laboratories Inc", "Teva Pharmaceuticals Usa Inc"], "atc_classification": [{"code": "S01AE03", "description": "SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFECTIVES: Fluoroquinolone"}, {"code": "S02AA15", "description": "SENSORY ORGANS: OTOLOGICALS: ANTIINFECTIVES: Antiinfective"}, {"code": "S03AA07", "description": "SENSORY ORGANS: OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS: ANTIINFECTIVES: Antiinfective"}, {"code": "J01MA02", "description": "ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolones"}], "availability_type": 1, "biotherapeutic": null, "black_box": 1, "black_box_warning": "1", "chirality": 2, "drug_type": 1, "first_approval": 1987, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL8", "molecule_properties": {"alogp": "1.58", "aromatic_rings": 2, "full_molformula": "C17H18FN3O3", "full_mwt": "331.35", "hba": 5, "hbd": 2, "heavy_atoms": 24, "mw_freebase": "331.35", "np_likeness_score": "-0.72", "num_ro5_violations": 0, "psa": "74.57", "qed_weighted": "0.89", "ro3_pass": "N", "rtb": 3}, "molecule_structures": {"canonical_smiles": "O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O", "molfile": "\n RDKit 2D\n\n 24 27 0 0 0 0 0 0 0 0999 V2000\n 2.1792 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2625 0.6625 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3542 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3542 0.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2625 -1.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1792 0.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5583 0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4708 0.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2625 1.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.5583 -1.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1167 -1.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.4708 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.3833 0.6625 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 2.0167 2.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.7000 2.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2625 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2083 1.7083 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 3.1375 -2.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4125 -1.3917 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 4.2625 -0.7000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n -3.2958 0.1083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.3833 1.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -4.2083 0.6333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.2958 2.2250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 6 1 0\n 3 5 1 0\n 4 2 1 0\n 5 1 1 0\n 6 1 2 0\n 7 4 1 0\n 8 7 2 0\n 9 2 1 0\n 10 3 1 0\n 11 1 1 0\n 12 10 2 0\n 13 8 1 0\n 14 9 1 0\n 15 9 1 0\n 16 5 2 0\n 17 24 1 0\n 18 11 2 0\n 19 12 1 0\n 20 11 1 0\n 21 13 1 0\n 22 13 1 0\n 23 21 1 0\n 24 22 1 0\n 3 4 2 0\n 14 15 1 0\n 12 8 1 0\n 23 17 1 0\nM END\n", "standard_inchi": "InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)", "standard_inchi_key": "MYSWGUAQZAJSOK-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "BAY O 9867 FREE BASE", "syn_type": "RESEARCH_CODE", "synonyms": "BAY O 9867 FREE BASE"}, {"molecule_synonym": "BAY-O-9867 FREE BASE", "syn_type": "RESEARCH_CODE", "synonyms": "BAY-O-9867 FREE BASE"}, {"molecule_synonym": "BAY Q 3939", "syn_type": "RESEARCH_CODE", "synonyms": "BAY Q 3939"}, {"molecule_synonym": "BAY-Q-3939", "syn_type": "RESEARCH_CODE", "synonyms": "BAY-Q-3939"}, {"molecule_synonym": "BAYQ3939", "syn_type": "RESEARCH_CODE", "synonyms": "BAYQ3939"}, {"molecule_synonym": "Cetraxal", "syn_type": "TRADE_NAME", "synonyms": "CETRAXAL"}, {"molecule_synonym": "Cipro", "syn_type": "TRADE_NAME", "synonyms": "CIPRO"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "ATC", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "BAN", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "BNF", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "FDA", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "INN", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "JAN", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "MERCK_INDEX", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "OTHER", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "TRADE_NAME", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "USAN", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin", "syn_type": "USP", "synonyms": "CIPROFLOXACIN"}, {"molecule_synonym": "Ciprofloxacin component of ciprodex", "syn_type": "TRADE_NAME", "synonyms": "CIPROFLOXACIN COMPONENT OF CIPRODEX"}, {"molecule_synonym": "Ciprofloxacine", "syn_type": "INN_FRENCH", "synonyms": "CIPROFLOXACINE"}, {"molecule_synonym": "Ciprofloxacino", "syn_type": "INN_SPANISH", "synonyms": "CIPROFLOXACINO"}, {"molecule_synonym": "Ciprofloxacinum", "syn_type": "OTHER", "synonyms": "CIPROFLOXACINUM"}, {"molecule_synonym": "NSC-758467", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-758467"}, {"molecule_synonym": "Otiprio", "syn_type": "TRADE_NAME", "synonyms": "OTIPRIO"}, {"molecule_synonym": "Velmonit", "syn_type": "TRADE_NAME", "synonyms": "Velmonit"}], "ob_patent": "8318817", "oral": 1, "parenteral": 1, "prodrug": 0, "research_codes": ["BAY-O-9867 MONOHYDRATE", "BAY O 9867", "BAY Q 3939", "BAY O 9867 FREE BASE", "BAYQ3939", "BAY O 9867 MONOHYDRATE", "BAY-O-9867 FREE BASE", "NSC-758467", "BAY-O-9867", "BAY-Q-3939"], "rule_of_five": 1, "sc_patent": "US-8318817-B2", "synonyms": ["Ciprofloxacin (BAN, INN, JAN, MI, USAN, USP)", "Ciprofloxacin hydrochloride (JAN, USAN, USP)", "Ciprofloxacin hydrochloride hydrate (JAN)", "Ciprofloxacin hydrochloride monohydrate (MI)", ""], "topical": 1, "usan_stem": "-oxacin", "usan_stem_definition": "antibacterials (quinolone derivatives)", "usan_stem_substem": "-oxacin(-oxacin)", "usan_year": 1987, "withdrawn_flag": "0"}, {"applicants": ["Merck Research Laboratories Div Merck Co Inc"], "atc_classification": [{"code": "J01MA06", "description": "ANTIINFECTIVES FOR SYSTEMIC USE: ANTIBACTERIALS FOR SYSTEMIC USE: QUINOLONE ANTIBACTERIALS: Fluoroquinolone"}, {"code": "S01AE02", "description": "SENSORY ORGANS: OPHTHALMOLOGICALS: ANTIINFECTIVES: Fluoroquinolones"}], "availability_type": 0, "biotherapeutic": null, "black_box": 1, "black_box_warning": "1", "chirality": 2, "drug_type": 1, "first_approval": 1986, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL9", "molecule_properties": {"alogp": "1.27", "aromatic_rings": 2, "full_molformula": "C16H18FN3O3", "full_mwt": "319.34", "hba": 5, "hbd": 2, "heavy_atoms": 23, "mw_freebase": "319.34", "np_likeness_score": "-0.97", "num_ro5_violations": 0, "psa": "74.57", "qed_weighted": "0.89", "ro3_pass": "N", "rtb": 3}, "molecule_structures": {"canonical_smiles": "CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)cc21", "molfile": "\n RDKit 2D\n\n 23 25 0 0 0 0 0 0 0 0999 V2000\n 6.6500 -5.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4000 -5.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0250 -5.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.4000 -4.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6500 -4.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0250 -4.4875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7792 -4.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1542 -4.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.7792 -5.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2625 -5.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.1542 -5.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5417 -4.4917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0250 -6.6042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2917 -3.7875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.2542 -6.5875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5417 -5.8917 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0\n 7.8500 -5.5375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 6.0250 -3.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9167 -4.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5417 -3.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.3042 -4.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.9042 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.6167 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 3 1 0\n 3 1 1 0\n 4 6 1 0\n 5 1 2 0\n 6 5 1 0\n 7 4 2 0\n 8 7 1 0\n 9 2 2 0\n 10 1 1 0\n 11 9 1 0\n 12 8 1 0\n 13 3 2 0\n 14 22 1 0\n 15 10 2 0\n 16 11 1 0\n 17 10 1 0\n 18 6 1 0\n 19 12 1 0\n 20 12 1 0\n 21 19 1 0\n 22 20 1 0\n 23 18 1 0\n 2 4 1 0\n 11 8 2 0\n 14 21 1 0\nM END\n", "standard_inchi": "InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)", "standard_inchi_key": "OGJPXUAPXNRGGI-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Baccidal", "syn_type": "TRADE_NAME", "synonyms": "Baccidal"}, {"molecule_synonym": "Chibroxin", "syn_type": "TRADE_NAME", "synonyms": "CHIBROXIN"}, {"molecule_synonym": "MK-366", "syn_type": "RESEARCH_CODE", "synonyms": "MK-366"}, {"molecule_synonym": "Norfloxacin", "syn_type": "ATC", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "BAN", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "BNF", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "FDA", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "INN", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "JAN", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "MERCK_INDEX", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "OTHER", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "USAN", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacin", "syn_type": "USP", "synonyms": "NORFLOXACIN"}, {"molecule_synonym": "Norfloxacine", "syn_type": "INN_FRENCH", "synonyms": "NORFLOXACINE"}, {"molecule_synonym": "Norfloxacino", "syn_type": "INN_SPANISH", "synonyms": "NORFLOXACINO"}, {"molecule_synonym": "Noroxin", "syn_type": "TRADE_NAME", "synonyms": "NOROXIN"}, {"molecule_synonym": "NSC-757250", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-757250"}, {"molecule_synonym": "Quinabic", "syn_type": "TRADE_NAME", "synonyms": "Quinabic"}, {"molecule_synonym": "Utinor", "syn_type": "TRADE_NAME", "synonyms": "UTINOR"}], "ob_patent": null, "oral": 1, "parenteral": 0, "prodrug": 0, "research_codes": ["NSC-757250", "MK-366"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Norfloxacin (BAN, INN, JAN, MI, USAN, USP)", ""], "topical": 1, "usan_stem": "-oxacin", "usan_stem_definition": "antibacterials (quinolone derivatives)", "usan_stem_substem": "-oxacin(-oxacin)", "usan_year": 1984, "withdrawn_flag": "0"}, {"applicants": null, "atc_code_description": null, "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "1.0", "molecule_chembl_id": "CHEMBL269538", "molecule_properties": {"alogp": "3.03", "aromatic_rings": 3, "full_molformula": "C13H12N2O", "full_mwt": "212.25", "hba": 2, "hbd": 1, "heavy_atoms": 16, "mw_freebase": "212.25", "np_likeness_score": "0.29", "num_ro5_violations": 0, "psa": "37.91", "qed_weighted": "0.67", "ro3_pass": "N", "rtb": 1}, "molecule_structures": {"canonical_smiles": "COc1ccc2c(c1)[nH]c1c(C)nccc12", "molfile": "\n RDKit 2D\n\n 16 18 0 0 0 0 0 0 0 0999 V2000\n 2.4942 -0.0844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 5.3276 -0.8394 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 7.3541 0.0871 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 5.7401 0.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.9151 0.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 5.9951 -0.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.6602 -0.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.8021 -0.5260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.8532 -0.5260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 4.3631 1.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 6.2922 1.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.3012 0.0871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.5561 0.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0991 0.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 7.0570 -1.3106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.2393 -0.8691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1 12 1 0\n 1 16 1 0\n 2 6 1 0\n 2 7 1 0\n 3 8 1 0\n 3 14 2 0\n 4 5 1 0\n 4 6 1 0\n 4 11 2 0\n 5 7 1 0\n 5 10 2 0\n 6 8 2 0\n 7 9 2 0\n 8 15 1 0\n 9 12 1 0\n 10 13 1 0\n 11 14 1 0\n 12 13 2 0\nM END", "standard_inchi": "InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3", "standard_inchi_key": "BXNJHAXVSOCGBA-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Harmine", "syn_type": "MERCK_INDEX", "synonyms": "HARMINE"}, {"molecule_synonym": "Harmine", "syn_type": "OTHER", "synonyms": "HARMINE"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": null, "rule_of_five": 1, "sc_patent": null, "synonyms": ["Harmine (MI)", ""], "topical": 0, "usan_stem": null, "usan_stem_definition": null, "usan_stem_substem": null, "usan_year": null, "withdrawn_flag": "0"}, {"applicants": null, "atc_code_description": null, "availability_type": null, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 2, "drug_type": 1, "first_approval": null, "first_in_class": 0, "helm_notation": null, "max_phase": "2.0", "molecule_chembl_id": "CHEMBL6318", "molecule_properties": {"alogp": "7.13", "aromatic_rings": 3, "full_molformula": "C28H30INO", "full_mwt": "523.46", "hba": 2, "hbd": 0, "heavy_atoms": 31, "mw_freebase": "523.46", "np_likeness_score": "-0.83", "num_ro5_violations": 2, "psa": "12.47", "qed_weighted": "0.23", "ro3_pass": "N", "rtb": 8}, "molecule_structures": {"canonical_smiles": "CC/C(=C(\\c1ccc(I)cc1)c1ccc(OCCN2CCCC2)cc1)c1ccccc1", "molfile": "\n RDKit 2D\n\n 31 34 0 0 0 0 0 0 0 0999 V2000\n -1.2458 -0.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.0833 -0.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8333 0.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8333 -1.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.4667 2.9958 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5208 0.1625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2458 0.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -1.2458 -1.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0125 -1.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0125 0.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0125 -2.7042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.0125 1.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4000 -1.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8333 -2.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.8333 1.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4000 0.8333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4000 -3.4375 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0\n -2.4958 -1.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.4000 2.2833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1.6500 2.9958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 1.2375 2.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.0042 3.5958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.8792 2.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.1083 0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.3375 0.1625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.5083 -1.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.7417 3.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 3.6792 2.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -2.5208 1.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.7458 0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -3.3375 1.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 1 2 0\n 3 1 1 0\n 4 1 1 0\n 5 20 1 0\n 6 2 1 0\n 7 3 1 0\n 8 4 2 0\n 9 4 1 0\n 10 3 2 0\n 11 13 1 0\n 12 16 2 0\n 13 9 2 0\n 14 8 1 0\n 15 7 2 0\n 16 10 1 0\n 17 11 1 0\n 18 2 1 0\n 19 12 1 0\n 20 21 1 0\n 21 19 1 0\n 22 5 1 0\n 23 5 1 0\n 24 6 2 0\n 25 6 1 0\n 26 18 1 0\n 27 22 1 0\n 28 23 1 0\n 29 24 1 0\n 30 25 2 0\n 31 30 1 0\n 14 11 2 0\n 15 12 1 0\n 29 31 2 0\n 27 28 1 0\nM END\n", "standard_inchi": "InChI=1S/C28H30INO/c1-2-27(22-8-4-3-5-9-22)28(23-10-14-25(29)15-11-23)24-12-16-26(17-13-24)31-21-20-30-18-6-7-19-30/h3-5,8-17H,2,6-7,18-21H2,1H3/b28-27-", "standard_inchi_key": "JJKOTMDDZAJTGQ-DQSJHHFOSA-N"}, "molecule_synonyms": [{"molecule_synonym": "CB 7432", "syn_type": "RESEARCH_CODE", "synonyms": "CB 7432"}, {"molecule_synonym": "CB-7432", "syn_type": "RESEARCH_CODE", "synonyms": "CB-7432"}, {"molecule_synonym": "CB7432", "syn_type": "RESEARCH_CODE", "synonyms": "CB7432"}, {"molecule_synonym": "Idoxifene", "syn_type": "USAN", "synonyms": "Idoxifene"}, {"molecule_synonym": "Idoxifene", "syn_type": "BAN", "synonyms": "IDOXIFENE"}, {"molecule_synonym": "Idoxifene", "syn_type": "INN", "synonyms": "IDOXIFENE"}, {"molecule_synonym": "Idoxifeno", "syn_type": "INN_SPANISH", "synonyms": "IDOXIFENO"}, {"molecule_synonym": "SB-223030", "syn_type": "RESEARCH_CODE", "synonyms": "SB-223030"}, {"molecule_synonym": "SB223030", "syn_type": "RESEARCH_CODE", "synonyms": "SB223030"}], "ob_patent": null, "oral": 0, "parenteral": 0, "prodrug": 0, "research_codes": ["CB 7432", "CB-7432", "CB7432", "SB-223030", "SB223030"], "rule_of_five": 0, "sc_patent": null, "synonyms": ["Idoxifene (BAN, INN, USAN, USAN)", ""], "topical": 0, "usan_stem": "-ifene", "usan_stem_definition": "antiestrogens of the clomifene and tamoxifen groups", "usan_stem_substem": "-ifene(-ifene)", "usan_year": 1996, "withdrawn_flag": "0"}, {"applicants": ["Prinston Pharmaceutical Inc", "Granules Pharmaceuticals Inc", "Neos Therapeutics Inc", "Tris Pharma Inc", "Alkem Laboratories Ltd", "Teva Pharmaceuticals Usa", "Actavis Laboratories Fl Inc", "Impax Laboratories Inc", "Aurolife Pharma Llc", "Teva Pharmaceuticals Usa Inc"], "atc_classification": [{"code": "N06BA01", "description": "NERVOUS SYSTEM: PSYCHOANALEPTICS: PSYCHOSTIMULANTS, AGENTS USED FOR ADHD AND NOOTROPICS: Centrally acting sympathomimetics"}], "availability_type": 1, "biotherapeutic": null, "black_box": 1, "black_box_warning": "1", "chirality": 0, "drug_type": 1, "first_approval": 1955, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL405", "molecule_properties": {"alogp": "1.58", "aromatic_rings": 1, "full_molformula": "C9H13N", "full_mwt": "135.21", "hba": 1, "hbd": 1, "heavy_atoms": 10, "mw_freebase": "135.21", "np_likeness_score": "-0.02", "num_ro5_violations": 0, "psa": "26.02", "qed_weighted": "0.65", "ro3_pass": "Y", "rtb": 2}, "molecule_structures": {"canonical_smiles": "CC(N)Cc1ccccc1", "molfile": "\n RDKit 2D\n\n 10 10 0 0 0 0 0 0 0 0999 V2000\n 1.5625 0.7125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.7792 0.7208 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9500 0.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1792 0.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.9542 -0.3542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3292 0.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2.1792 -0.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 0.3375 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2833 0.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n -0.2833 -0.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 2 4 1 0\n 3 1 1 0\n 4 1 1 0\n 5 3 2 0\n 6 3 1 0\n 7 4 1 0\n 8 5 1 0\n 9 6 2 0\n 10 8 2 0\n 9 10 1 0\nM END", "standard_inchi": "InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3", "standard_inchi_key": "KWTSXDURSIMDCE-UHFFFAOYSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Adzenys er", "syn_type": "TRADE_NAME", "synonyms": "ADZENYS ER"}, {"molecule_synonym": "Adzenys xr-odt", "syn_type": "TRADE_NAME", "synonyms": "ADZENYS XR-ODT"}, {"molecule_synonym": "Amfetamin", "syn_type": "OTHER", "synonyms": "AMFETAMIN"}, {"molecule_synonym": "Amfetamine", "syn_type": "ATC", "synonyms": "AMFETAMINE"}, {"molecule_synonym": "Amfetamine", "syn_type": "INN", "synonyms": "AMFETAMINE"}, {"molecule_synonym": "Amfetamine", "syn_type": "OTHER", "synonyms": "AMFETAMINE"}, {"molecule_synonym": "Amphetamine", "syn_type": "FDA", "synonyms": "AMPHETAMINE"}, {"molecule_synonym": "Amphetamine", "syn_type": "MERCK_INDEX", "synonyms": "AMPHETAMINE"}, {"molecule_synonym": "Amphetamine", "syn_type": "OTHER", "synonyms": "AMPHETAMINE"}, {"molecule_synonym": "Amphetamine, dl-", "syn_type": "OTHER", "synonyms": "AMPHETAMINE, DL-"}, {"molecule_synonym": "Amphetamine resin complex", "syn_type": "FDA", "synonyms": "AMPHETAMINE RESIN COMPLEX"}, {"molecule_synonym": "Anfetamina", "syn_type": "INN_SPANISH", "synonyms": "ANFETAMINA"}, {"molecule_synonym": "Dyanavel", "syn_type": "OTHER", "synonyms": "DYANAVEL"}, {"molecule_synonym": "Dyanavel xr", "syn_type": "TRADE_NAME", "synonyms": "DYANAVEL XR"}, {"molecule_synonym": "Mydayis (mixed salts of a single entity)", "syn_type": "TRADE_NAME", "synonyms": "MYDAYIS (MIXED SALTS OF A SINGLE ENTITY)"}, {"molecule_synonym": "Norephedrane", "syn_type": "OTHER", "synonyms": "NOREPHEDRANE"}, {"molecule_synonym": "NSC-27159", "syn_type": "RESEARCH_CODE", "synonyms": "NSC-27159"}], "ob_patent": "8062667", "oral": 1, "parenteral": 0, "prodrug": 0, "research_codes": ["NSC-27159", "NSC-170999"], "rule_of_five": 1, "sc_patent": "US-8062667-B2", "synonyms": ["Amphetamine sulfate (MI)", "Amfetamine (INN)", "Amphetamine (MI)", ""], "topical": 0, "usan_stem": null, "usan_stem_definition": null, "usan_stem_substem": null, "usan_year": null, "withdrawn_flag": "0"}, {"applicants": ["Sandoz Inc", "Endo Operations Ltd", "Ani Pharmaceuticals Inc", "Watson Laboratories Inc An Indirect Wholly Owned Sub Of Teva Pharmaceuticals Usa Inc", "Watson Laboratories Inc", "Astrazeneca Pharmaceuticals Lp", "Zydus Lifesciences Global Fze", "Hikma International Pharmaceuticals Llc", "Riconpharma Llc", "Rubicon Research Private Ltd"], "atc_classification": [{"code": "C05AE02", "description": "CARDIOVASCULAR SYSTEM: VASOPROTECTIVES: AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE: Muscle relaxant"}, {"code": "C01DA58", "description": "CARDIOVASCULAR SYSTEM: CARDIAC THERAPY: VASODILATORS USED IN CARDIAC DISEASES: Organic nitrate"}, {"code": "C01DA08", "description": "CARDIOVASCULAR SYSTEM: CARDIAC THERAPY: VASODILATORS USED IN CARDIAC DISEASES: Organic nitrates"}], "availability_type": 1, "biotherapeutic": null, "black_box": 0, "black_box_warning": "0", "chirality": 1, "drug_type": 1, "first_approval": 1986, "first_in_class": 0, "helm_notation": null, "max_phase": "4.0", "molecule_chembl_id": "CHEMBL6622", "molecule_properties": {"alogp": "-1.06", "aromatic_rings": 0, "full_molformula": "C6H8N2O8", "full_mwt": "236.14", "hba": 8, "hbd": 0, "heavy_atoms": 16, "mw_freebase": "236.14", "np_likeness_score": "-0.02", "num_ro5_violations": 0, "psa": "123.20", "qed_weighted": "0.45", "ro3_pass": "N", "rtb": 4}, "molecule_structures": {"canonical_smiles": "O=[N+]([O-])O[C@H]1CO[C@H]2[C@@H]1OC[C@H]2O[N+](=O)[O-]", "molfile": "\n RDKit 2D\n\n 18 19 0 0 0 0 0 0 0 0999 V2000\n 10.7582 -23.3680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 10.7582 -22.5466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9775 -23.6194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4929 -22.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.9755 -22.2873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 9.4874 -21.6213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7032 -21.8796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.7066 -22.7053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0\n 8.0439 -23.1908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.1331 -24.0074 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 8.8881 -24.3412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 7.4738 -24.4957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 8.9078 -23.5464 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 11.4242 -22.0656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 10.3848 -21.5799 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0\n 12.1737 -22.4018 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0\n 12.8432 -21.9191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 12.2609 -23.2174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0\n 1 2 1 0\n 2 5 1 0\n 4 3 1 0\n 3 1 1 0\n 4 5 1 0\n 5 6 1 0\n 6 7 1 0\n 7 8 1 0\n 8 4 1 0\n 8 9 1 6\n 9 10 1 0\n 10 11 2 0\n 10 12 1 0\n 2 14 1 1\n 14 16 1 0\n 16 17 2 0\n 16 18 1 0\n 5 15 1 1\n 4 13 1 1\nM CHG 4 10 1 12 -1 16 1 18 -1\nM END", "standard_inchi": "InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1", "standard_inchi_key": "MOYKHGMNXAOIAT-JGWLITMVSA-N"}, "molecule_synonyms": [{"molecule_synonym": "Angitak", "syn_type": "TRADE_NAME", "synonyms": 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DINITRATE"}, {"molecule_synonym": "Diluted-isosorbide dinitrate", "syn_type": "OTHER", "synonyms": "DILUTED-ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Diluted isosorbide dinitrate rs", "syn_type": "USP", "synonyms": "DILUTED ISOSORBIDE DINITRATE RS"}, {"molecule_synonym": "Dinitrate d'isosorbide", "syn_type": "INN_FRENCH", "synonyms": "DINITRATE D'ISOSORBIDE"}, {"molecule_synonym": "Dinitrato de isosorbida", "syn_type": "INN_SPANISH", "synonyms": "DINITRATO DE ISOSORBIDA"}, {"molecule_synonym": "Imtack", "syn_type": "TRADE_NAME", "synonyms": "IMTACK"}, {"molecule_synonym": "Isocard", "syn_type": "TRADE_NAME", "synonyms": "ISOCARD"}, {"molecule_synonym": "Isoket 10", "syn_type": "TRADE_NAME", "synonyms": "ISOKET 10"}, {"molecule_synonym": "Isoket 20", "syn_type": "TRADE_NAME", "synonyms": "ISOKET 20"}, {"molecule_synonym": "Isoket 5", "syn_type": "TRADE_NAME", "synonyms": "ISOKET 5"}, {"molecule_synonym": "Isoket ret 20", "syn_type": "TRADE_NAME", "synonyms": "ISOKET RET 20"}, {"molecule_synonym": "Isoket ret 40", "syn_type": "TRADE_NAME", "synonyms": "ISOKET RET 40"}, {"molecule_synonym": "Iso mack", "syn_type": "TRADE_NAME", "synonyms": "ISO MACK"}, {"molecule_synonym": "Isomannide dinitrate", "syn_type": "OTHER", "synonyms": "ISOMANNIDE DINITRATE"}, {"molecule_synonym": "Isomannide-dinitrate", "syn_type": "OTHER", "synonyms": "ISOMANNIDE-DINITRATE"}, {"molecule_synonym": "Isordil", "syn_type": "TRADE_NAME", "synonyms": "ISORDIL"}, {"molecule_synonym": "Isordil tembids", "syn_type": "TRADE_NAME", "synonyms": "ISORDIL TEMBIDS"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "ATC", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "BAN", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "BNF", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "FDA", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "INN", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "JAN", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "MERCK_INDEX", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "OTHER", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "TRADE_NAME", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "USAN", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate", "syn_type": "USP", "synonyms": "ISOSORBIDE DINITRATE"}, {"molecule_synonym": "Isosorbide dinitrate component of bidil", "syn_type": "TRADE_NAME", "synonyms": "ISOSORBIDE DINITRATE COMPONENT OF BIDIL"}, {"molecule_synonym": "Isosorbide dinitrate, diluted", "syn_type": "OTHER", "synonyms": "ISOSORBIDE DINITRATE, DILUTED"}, {"molecule_synonym": "Isosorbide 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"TRADE_NAME", "synonyms": "SORBIDILAT"}, {"molecule_synonym": "Sorbid sa", "syn_type": "TRADE_NAME", "synonyms": "SORBID SA"}, {"molecule_synonym": "Sorbitrate", "syn_type": "TRADE_NAME", "synonyms": "SORBITRATE"}, {"molecule_synonym": "Vascardin", "syn_type": "TRADE_NAME", "synonyms": "VASCARDIN"}], "ob_patent": null, "oral": 1, "parenteral": 0, "prodrug": 1, "research_codes": ["C01DA08", "NSC-80038"], "rule_of_five": 1, "sc_patent": null, "synonyms": ["Diluted isosorbide dinitrate (USP)", "Diluted isosorbide dinitrate rs (USP)", "Isosorbide dinitrate (BAN, INN, JAN, MI, USAN, USP)", ""], "topical": 1, "usan_stem": null, "usan_stem_definition": null, "usan_stem_substem": null, "usan_year": 1966, "withdrawn_flag": "0"}], "page_meta": {"limit": 20, "next": "/chembl/api/data/drug.json?limit=20&offset=20", "offset": 0, "previous": null, "total_count": 16093}}